how is the sizing on outerwear? I normally wear a Medium in most items and a 48 IT suit jacket, but oftentimes a 50 IT in outerwear. Would a size 50 in a bomber or wool field jacket be okay? For reference, I am 6'1" with a 38" chest and 31" waist. Thanks!

Honestly man, this really varies by piece and how you intend to wear it.

With a bomber, if you plan on having heavy layers below it normally, then size up. Otherwise, go true to size.

Field Jacket is probably cut a little more generous than the bomber to begin with, I wouldn't size up there.